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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-02-04 10:21:51 UTC

Update Date

2022-03-07 02:51:13 UTC

HMDB ID

HMDB0011678

Secondary Accession Numbers

HMDB11678

Metabolite Identification

Common Name

Geranylgeranylcysteine

Description

Geranylgeranylcysteine is a modified thioether amino acid in which an isoprenyl group (geranylgeranyl) has been attached to the sulfhydryl group of cysteine through a thioether bond. Geranylgeranylcysteine is typically formed through posttranslational (prenylation) protein modification whereupon degradation of the parent protein leaves the modified (prenylated) amino acid. Prenylation is a relatively recently discovered post-translational modification of proteins that directs cytosollic proteins to membranes while at the same time activating them functionally. The change in hydrophobicity that is essential for membrane binding is done via the covalent attachment of a polyisoprene (such as a farnesyl or geranylgeranyl group) to a C-terminal cysteine by a thioether bond. Prenylated proteins can comprise up to 2% of total cellular protein. Prenylcysteine lyase is an enzyme that is capable of cleaving the thiother bond in prenylcysteines and is used to help in the turnover of prenylated proteins. Prenylcysteine lyase deficiency leads to the accumulation of farnesylcysteine and geranylgeranylcysteine in brain and liver. (PMID: 9287348 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241201502D          

 28 27  0  0  1  0            999 V2000
    3.1152  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4021  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5455  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2599  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9744  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -13.6428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.0553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2613  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9757  -14.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1152  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -12.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -15.2928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 21  1  1  0  0  0  0
 22 18  2  0  0  0  0
 17 23  1  6  0  0  0
 24 23  1  0  0  0  0
 25 15  2  0  0  0  0
 26 13  1  0  0  0  0
 27  9  1  0  0  0  0
 28  5  1  0  0  0  0
M  END

HMDB0011678
     RDKit          3D
Geranylgeranylcysteine
 65 64  0  0  0  0  0  0  0  0999 V2000
    7.2090    0.6262    2.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    0.1158    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8698   -0.3687    1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5440    0.1017    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8684   -0.4052   -0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -1.5196   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717   -1.1101   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -2.1545   -1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.1618   -1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    0.4990   -1.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    1.1931   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813    1.5002   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    2.3772   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.0177    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341    1.3216   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    0.0047   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7521    0.2922   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1412    1.1401   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -0.2276    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663    0.0073    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4507    0.7312   -0.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175   -0.5735    0.9077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -0.3364    0.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0939   -1.6845    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8398   -2.7519    1.9317 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9892    0.2496    1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2511    0.4561    2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3265    0.5812    2.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1907    0.2324    3.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9540    0.3562    3.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0935    1.7456    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330   -0.2658    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2604    0.2702    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9177   -1.4228    0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5606    0.4372    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9164   -0.7754   -0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8333    0.4671   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993   -2.0406   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599   -2.2515   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0179   -3.1340   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.1678   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0915   -2.0173   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913    0.9888   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    1.1919   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.3867   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434    0.4932    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    2.1154    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.7626   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    3.2370   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    2.7851   -2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.3823    1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    1.8686    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.9324   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712   -0.5118   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2047   -0.6876    0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    1.4627   -2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.0959   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    0.5821   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644   -0.8684    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7007   -1.1719    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5722    0.3103   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7381   -2.1583   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1929   -1.5251    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7632   -1.9382    3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6620    1.5157    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 26 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 24 63  1  0
 25 64  1  0
 28 65  1  0
M  END


  Mrv0541 02241201502D          

 28 27  0  0  1  0            999 V2000
    3.1152  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4021  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5455  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2599  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9744  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -13.6428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.0553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2613  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9757  -14.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1152  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -12.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -15.2928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 21  1  1  0  0  0  0
 22 18  2  0  0  0  0
 17 23  1  6  0  0  0
 24 23  1  0  0  0  0
 25 15  2  0  0  0  0
 26 13  1  0  0  0  0
 27  9  1  0  0  0  0
 28  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011678

> <DATABASE_NAME>
hmdb

> <SMILES>
SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1

> <INCHI_KEY>
UBCKUGRWFMEXIF-WONWMLGISA-N

> <FORMULA>
C23H37NO3S

> <MOLECULAR_WEIGHT>
407.61

> <EXACT_MASS>
407.249414745

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
48.78785754192435

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
5.654119356

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.049435375930052

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.041595471416822

> <JCHEM_PKA_STRONGEST_BASIC>
1.452563358758466

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
123.67839999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011678
     RDKit          3D
Geranylgeranylcysteine
 65 64  0  0  0  0  0  0  0  0999 V2000
    7.2090    0.6262    2.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    0.1158    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8698   -0.3687    1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5440    0.1017    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8684   -0.4052   -0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -1.5196   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717   -1.1101   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -2.1545   -1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.1618   -1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    0.4990   -1.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    1.1931   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813    1.5002   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    2.3772   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.0177    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341    1.3216   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    0.0047   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7521    0.2922   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1412    1.1401   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -0.2276    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663    0.0073    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4507    0.7312   -0.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175   -0.5735    0.9077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -0.3364    0.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0939   -1.6845    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8398   -2.7519    1.9317 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9892    0.2496    1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2511    0.4561    2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3265    0.5812    2.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1907    0.2324    3.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9540    0.3562    3.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0935    1.7456    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330   -0.2658    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2604    0.2702    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9177   -1.4228    0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5606    0.4372    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9164   -0.7754   -0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8333    0.4671   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993   -2.0406   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599   -2.2515   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0179   -3.1340   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.1678   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0915   -2.0173   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913    0.9888   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    1.1919   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.3867   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434    0.4932    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    2.1154    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.7626   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    3.2370   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    2.7851   -2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.3823    1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    1.8686    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.9324   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712   -0.5118   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2047   -0.6876    0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    1.4627   -2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.0959   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    0.5821   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644   -0.8684    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7007   -1.1719    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5722    0.3103   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7381   -2.1583   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1929   -1.5251    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7632   -1.9382    3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6620    1.5157    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 26 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 24 63  1  0
 25 64  1  0
 28 65  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.815 -26.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.149 -25.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.482 -26.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.816 -25.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.150 -26.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.484 -25.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.817 -26.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.151 -25.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.485 -26.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.818 -25.467   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.152 -26.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.486 -25.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.819 -26.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.153 -25.467   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.487 -26.237   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      25.820 -25.467   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      27.154 -26.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.488 -25.467   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      29.821 -26.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.481 -25.467   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.815 -27.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.488 -23.927   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      27.154 -27.777   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0      28.488 -28.547   0.000  0.00  0.00           S+0
HETATM   25  O   UNK     0      24.487 -27.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.819 -27.777   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.485 -27.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.150 -27.777   0.000  0.00  0.00           C+0
CONECT    1    2   20   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22   18                                                            
CONECT   23   17   24                                                       
CONECT   24   23                                                            
CONECT   25   15                                                            
CONECT   26   13                                                            
CONECT   27    9                                                            
CONECT   28    5                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0011678
HETATM    1  C1  UNL     1       7.209   0.626   2.889  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.537   0.116   1.538  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.870  -0.369   1.150  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.544   0.102   0.621  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.868  -0.405  -0.722  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.976  -1.520  -1.114  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.572  -1.110  -1.315  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.504  -2.154  -1.600  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.231   0.162  -1.250  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.791   0.499  -1.459  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.212   1.193  -0.238  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.781   1.500  -0.511  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.424   2.377  -1.656  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.201   1.018   0.234  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.634   1.322  -0.034  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.335   0.005  -0.296  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.752   0.292  -0.561  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.141   1.140  -1.689  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.667  -0.228   0.228  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.066   0.007   0.034  1.00  0.00           C  
HETATM   21  O1  UNL     1      -6.451   0.731  -0.915  1.00  0.00           O  
HETATM   22  N1  UNL     1      -7.017  -0.574   0.908  1.00  0.00           N  
HETATM   23  C21 UNL     1      -8.433  -0.336   0.712  1.00  0.00           C  
HETATM   24  C22 UNL     1      -9.094  -1.685   0.496  1.00  0.00           C  
HETATM   25  S1  UNL     1      -8.840  -2.752   1.932  1.00  0.00           S  
HETATM   26  C23 UNL     1      -8.989   0.250   1.972  1.00  0.00           C  
HETATM   27  O2  UNL     1      -8.251   0.456   2.969  1.00  0.00           O  
HETATM   28  O3  UNL     1     -10.326   0.581   2.079  1.00  0.00           O  
HETATM   29  H1  UNL     1       6.191   0.232   3.143  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.954   0.356   3.645  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.094   1.746   2.856  1.00  0.00           H  
HETATM   32  H4  UNL     1       9.533  -0.266   2.050  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.260   0.270   0.312  1.00  0.00           H  
HETATM   34  H6  UNL     1       8.918  -1.423   0.851  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.561   0.437   0.897  1.00  0.00           H  
HETATM   36  H8  UNL     1       7.916  -0.775  -0.788  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.833   0.467  -1.413  1.00  0.00           H  
HETATM   38  H10 UNL     1       6.299  -2.041  -2.047  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.960  -2.252  -0.264  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.018  -3.134  -1.599  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.744  -2.168  -0.810  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.092  -2.017  -2.621  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.891   0.989  -1.096  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.668   1.192  -2.317  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.168  -0.387  -1.660  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.243   0.493   0.627  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.752   2.115   0.014  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.159   1.763  -2.371  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.209   3.237  -1.347  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.348   2.785  -2.143  1.00  0.00           H  
HETATM   51  H23 UNL     1       0.079   0.382   1.062  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.113   1.869   0.784  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.729   1.932  -0.952  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.871  -0.512  -1.182  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.205  -0.688   0.581  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.213   1.463  -2.246  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.623   2.096  -1.397  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.728   0.582  -2.464  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.364  -0.868   1.073  1.00  0.00           H  
HETATM   60  H32 UNL     1      -6.701  -1.172   1.692  1.00  0.00           H  
HETATM   61  H33 UNL     1      -8.572   0.310  -0.158  1.00  0.00           H  
HETATM   62  H34 UNL     1      -8.738  -2.158  -0.432  1.00  0.00           H  
HETATM   63  H35 UNL     1     -10.193  -1.525   0.378  1.00  0.00           H  
HETATM   64  H36 UNL     1      -8.763  -1.938   3.093  1.00  0.00           H  
HETATM   65  H37 UNL     1     -10.662   1.516   1.848  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4    4
CONECT    3   32   33   34
CONECT    4    5   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8    9    9
CONECT    8   40   41   42
CONECT    9   10   43
CONECT   10   11   44   45
CONECT   11   12   46   47
CONECT   12   13   14   14
CONECT   13   48   49   50
CONECT   14   15   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   19   19
CONECT   18   56   57   58
CONECT   19   20   59
CONECT   20   21   21   22
CONECT   22   23   60
CONECT   23   24   26   61
CONECT   24   25   62   63
CONECT   25   64
CONECT   26   27   27   28
CONECT   28   65
END

HMDB0011678
     RDKit          3D
Geranylgeranylcysteine
 65 64  0  0  0  0  0  0  0  0999 V2000
    7.2090    0.6262    2.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    0.1158    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8698   -0.3687    1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5440    0.1017    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8684   -0.4052   -0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -1.5196   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717   -1.1101   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -2.1545   -1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.1618   -1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    0.4990   -1.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    1.1931   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813    1.5002   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    2.3772   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.0177    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341    1.3216   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    0.0047   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7521    0.2922   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1412    1.1401   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -0.2276    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663    0.0073    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4507    0.7312   -0.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175   -0.5735    0.9077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -0.3364    0.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0939   -1.6845    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8398   -2.7519    1.9317 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9892    0.2496    1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2511    0.4561    2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3265    0.5812    2.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1907    0.2324    3.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9540    0.3562    3.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0935    1.7456    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330   -0.2658    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2604    0.2702    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9177   -1.4228    0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5606    0.4372    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9164   -0.7754   -0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8333    0.4671   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2993   -2.0406   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599   -2.2515   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0179   -3.1340   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.1678   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0915   -2.0173   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913    0.9888   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    1.1919   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.3867   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434    0.4932    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    2.1154    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.7626   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    3.2370   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    2.7851   -2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.3823    1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    1.8686    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.9324   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712   -0.5118   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2047   -0.6876    0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    1.4627   -2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.0959   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    0.5821   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644   -0.8684    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7007   -1.1719    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5722    0.3103   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7381   -2.1583   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1929   -1.5251    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7632   -1.9382    3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6620    1.5157    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 26 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 24 63  1  0
 25 64  1  0
 28 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
S-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-(e,e,e)-L-cysteine	HMDB
S-[(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl]- (9ci)-L-cysteine	HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulfanylpropanoate	Generator, HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoate	Generator, HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoic acid	Generator, HMDB

Chemical Formula

C₂₃H₃₇NO₃S

Average Molecular Weight

407.61

Monoisotopic Molecular Weight

407.249414745

IUPAC Name

(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

Traditional Name

(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

CAS Registry Number

169523-06-2

SMILES

SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1

InChI Key

UBCKUGRWFMEXIF-WONWMLGISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid or derivatives
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Alkylthiol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.58	ALOGPS
logP	5.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	1.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	123.68 m³·mol⁻¹	ChemAxon
Polarizability	48.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.28	30932474
DeepCCS	[M-H]-	198.922	30932474
DeepCCS	[M-2H]-	232.889	30932474
DeepCCS	[M+Na]+	208.117	30932474
AllCCS	[M+H]+	209.9	32859911
AllCCS	[M+H-H2O]+	207.7	32859911
AllCCS	[M+NH4]+	212.0	32859911
AllCCS	[M+Na]+	212.5	32859911
AllCCS	[M-H]-	203.6	32859911
AllCCS	[M+Na-2H]-	205.4	32859911
AllCCS	[M+HCOO]-	207.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Geranylgeranylcysteine	SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O	4339.7	Standard polar	33892256
Geranylgeranylcysteine	SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O	2765.2	Standard non polar	33892256
Geranylgeranylcysteine	SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O	3151.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Geranylgeranylcysteine,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C	3094.2	Semi standard non polar	33892256
Geranylgeranylcysteine,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O	3224.6	Semi standard non polar	33892256
Geranylgeranylcysteine,1TMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C	3056.5	Semi standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	3200.8	Semi standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	3122.2	Standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	3650.6	Standard polar	33892256
Geranylgeranylcysteine,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2984.4	Semi standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2940.6	Standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3469.0	Standard polar	33892256
Geranylgeranylcysteine,2TMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3175.4	Semi standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3146.0	Standard non polar	33892256
Geranylgeranylcysteine,2TMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3728.0	Standard polar	33892256
Geranylgeranylcysteine,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3113.4	Semi standard non polar	33892256
Geranylgeranylcysteine,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3110.5	Standard non polar	33892256
Geranylgeranylcysteine,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3316.4	Standard polar	33892256
Geranylgeranylcysteine,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C	3307.5	Semi standard non polar	33892256
Geranylgeranylcysteine,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O	3453.7	Semi standard non polar	33892256
Geranylgeranylcysteine,1TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C(C)(C)C	3264.0	Semi standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3602.4	Semi standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3510.5	Standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3695.0	Standard polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3401.6	Semi standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3306.8	Standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3616.8	Standard polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3605.6	Semi standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3501.7	Standard non polar	33892256
Geranylgeranylcysteine,2TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3773.5	Standard polar	33892256
Geranylgeranylcysteine,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3751.7	Semi standard non polar	33892256
Geranylgeranylcysteine,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3624.8	Standard non polar	33892256
Geranylgeranylcysteine,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C(=O)N([C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3483.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Geranylgeranylcysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-8889000000-3f81e03325547663218e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Geranylgeranylcysteine GC-MS (1 TMS) - 70eV, Positive	splash10-022l-9352500000-a735063f6d3013ad3130	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Geranylgeranylcysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 10V, Positive-QTOF	splash10-0a4i-2769600000-ec3a2eaceb3ae67eb426	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 20V, Positive-QTOF	splash10-0ads-4961000000-44253e7d991961cef89d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 40V, Positive-QTOF	splash10-0ar0-8950000000-13cfd8c2ae6c7a125a61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 10V, Negative-QTOF	splash10-0ab9-2017900000-84ecb7d4aa334cb77ecf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 20V, Negative-QTOF	splash10-059i-4329200000-97099be07e7e001431c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 40V, Negative-QTOF	splash10-008l-9350000000-4a227b58aca7450e328b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 10V, Positive-QTOF	splash10-052r-0192200000-5cc299ff4ab00e2154d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 20V, Positive-QTOF	splash10-00ei-2890000000-3dbfcbdc69c287f49fe6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 40V, Positive-QTOF	splash10-00m0-7900000000-ebaf835d361f6930eb39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 10V, Negative-QTOF	splash10-00di-0019000000-6bfbdf0cbf1824b2f5c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 20V, Negative-QTOF	splash10-071l-9855100000-cb7896acb5225696b6a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranylgeranylcysteine 40V, Negative-QTOF	splash10-0536-9262000000-74db85fe9f128c11af64	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028366

KNApSAcK ID

Not Available

Chemspider ID

30776596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481025

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhang L, Tschantz WR, Casey PJ: Isolation and characterization of a prenylcysteine lyase from bovine brain. J Biol Chem. 1997 Sep 12;272(37):23354-9. [PubMed:9287348 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Geranylgeranylcysteine (HMDB0011678)

MOL for HMDB0011678 (Geranylgeranylcysteine)

3D MOL for HMDB0011678 (Geranylgeranylcysteine)

3D SDF for HMDB0011678 (Geranylgeranylcysteine)

3D-SDF for HMDB0011678 (Geranylgeranylcysteine)

PDB for HMDB0011678 (Geranylgeranylcysteine)

3D PDB for HMDB0011678 (Geranylgeranylcysteine)

SMILES for HMDB0011678 (Geranylgeranylcysteine)

INCHI for HMDB0011678 (Geranylgeranylcysteine)

Structure for HMDB0011678 (Geranylgeranylcysteine)

3D Structure for HMDB0011678 (Geranylgeranylcysteine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra